154825-96-4

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Chemical Properties

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Uses

A novel intermediate of Fexofenadine (F322470).

Upstream product

• 115-46-8 C₁₈H₂₁NO 
• 43076-23-9 1-(4-bromophenyl)-4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butan-1-ol 
• 31469-15-5 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene 
• 154825-97-5 methyl 2-(4-bromophenyl)-2,2-dimethylacetate 
• 927-74-2 3-Butyn-1-ol 
• 32454-35-6 2-(4-bromophenyl)-2-methylpropionic acid 
• 71-43-2 benzene 
• 547-63-7 Methyl isobutyrate 
• 4559-96-0 1-(4-bromophenyl)-4-chlorobutan-1-one 
• 108-86-1 bromobenzene 
• 154477-55-1 methyl 2-(4-(4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoate 
• 169032-12-6 2-[4-(1-Ethylendioxo-4-chlorobutyl)phenyl]isobutyl acetate 
• 252022-31-4 Methyl 2-[4-(1-ethylendioxo-4-chlorobutyl)phenyl]isobutyrate 
• 169032-14-8 2-[4-(1-Ethylendioxo-4-chlorobutyl)phenyl]isobutyric acid 

Downstream Products

• 83799-24-0 fexofenadine 
• 138452-21-8 fexofenadine hydrochloride 
• 154477-55-1 methyl 2-(4-(4-(4-(hydroxydiphenylmethyl)piperidin-1-yl)butanoyl)phenyl)-2-methylpropanoate 

Relevant academic research and scientific papers

Preparation method of fexofenadine

The invention provides a preparation method of fexofenadine, which comprises the following steps: by using bromobenzene as a raw material, carrying out Friedel-Crafts acylation reaction to obtain 4'-bromo-4-chlorophenone ; enabling 4'-bromo-4-chlorobutanone and 1-methoxy-1-(trimethylsiloxy)-2-methyl-1-propene to subjected to coupling reaction to obtain 2-[4-(4 -chloro-1-butyryl)phenyl]-2-methyl methyl propionate; and sequentially carrying out N-alkylation, carbonyl reduction and alkaline hydrolysis on 2-[4-(4 -chloro-1-butyryl)phenyl]-2-methylpropanoate to obtain fexofenadine. The method has the advantages of cheap and easily available raw materials, easiness in operation, high yield, low cost, no meta-isomer, suitability for industrial production and the like.

METHODS AND COMPOSITIONS FOR TREATING INFECTION

Provided herein are compositions and methods for treating or preventing infection.

Repurposing the antihistamine terfenadine for antimicrobial activity against staphylococcus aureus

Staphylococcus aureus is a rapidly growing health threat in the U.S., with resistance to several commonly prescribed treatments. A high-throughput screen identified the antihistamine terfenadine to possess, previously unreported, antimicrobial activity against S. aureus and other Gram-positive bacteria. In an effort to repurpose this drug, structure-activity relationship studies yielded 84 terfenadine-based analogues with several modifications providing increased activity versus S. aureus and other bacterial pathogens, including Mycobacterium tuberculosis. Mechanism of action studies revealed these compounds to exert their antibacterial effects, at least in part, through inhibition of the bacterial type II topoisomerases. This scaffold suffers from hERG liabilities which were not remedied through this round of optimization; however, given the overall improvement in activity of the set, terfenadine-based analogues provide a novel structural class of antimicrobial compounds with potential for further characterization as part of the continuing process to meet the current need for new antibiotics.

PREPARATION OF 2-(4-BROMOPHENYL)-2-METHYLPROPANOIC ACID

Selective bromination of 2-methyl-2-phenylpropanoic acid in aqueous medium is described to obtain pure 2-(4-bromophenyl)-2-methylpropanoic acid, which is a useful key intermediate in the process of manufacturing pure fexofenadine.

Preparation of 2-(4-bromophenyl)-2-methylpropanoic acid

Selective bromination of 2-methyl-2-phenytpropanoic acid on aqueous medium is described to obtain pure 2-(4-bromophenyl)-2-methylpropanoic acid, which is a useful key intermediate in the process of manufacturing pure fexofenadine.

PROCESS FOR PREPARING FEXOFENADINE

A process for preparing fexofenadine is described, which provides for the hydrolysis of 4-[4-[4-(hydroxydiphenylmethyl)-l-piperidyl]-l-oxobutyl]-α,α- dimethylbenzeneacetic acid-alkyl ester, in a mixture of water and optionally an organic solvent, in the presence of a base; the carboxylate salt of 4- [4- [4- (hydroxydiphenylmethyl)- 1 -piperidyl] - 1 -oxobutyl] -α,α -dimethylbenzeneacetic acid is thus obtained, which is directly reduced as carboxylate in a basic environment with hydrogen in the presence of a suitable hydrogenation catalyst to give the carboxylate of fexofenadine, which is precipitated by neutralisation of the solution.

INDUSTRIAL PROCESS OF FEXOFENADINE HYDROCHLORIDE WITH CONTROLLED SIDE PRODUCTS

The present invention relates to a process for the preparation of Anhydrous Fexofenadine Hydrochloride with controlled level of side products. Another aspect of the present invention is purification of Fexofenadine base free of meta isomer of fexofenadine base and fexofenadinone.

AN IMPROVED PROCESS FOR THE PREPARATION OF HIGHLY PURE FEXOFENADINE

The present invention provides an improved process for the preparation of highly pure 4-[1-hydroxy-4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-butyl]-α,α-dimethylbenzene acetic acid (fexofenadine) of Formula (I), or its salts thereof.

INTERMEDIATES USEFUL FOR THE PREPARATION OF ANTIHISTAMINIC PIPERIDINE DERIVATIVE

The present invention relates to process for preparing antihistaminic piperidine derivative, specifically fexofenadine and its pharmaceutically acceptable salts by using novel synthetic intermediates of following formula (I), wherein R is lower alkyl; R2 is H, cyclopropyl, R1is alkyl, 4-(hydroxy-dipheτiyl-methyl)-piperidin-l-yl.

Process for production of piperidine derivatives

Processes are disclosed for preparing piperidine derivative compounds of the formulae I, II or III: The processes involve reacting a compound of formula Ia, IIa or IIIa with isobutyrate or an isobutyrate equivalent.